Treatment of cellulosic textiles with 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, zinc nitrate and a sequestering agent

ABSTRACT

A FINISH FOR CELLULOSIC TEXTILE MATERIALS TO GIVE A WRINKLE RESISTANT AND PERMANENT CREASE TO SAID TEXTILE MATERIALS, WHEREIN THE FINISH CONTAINS A SEQUESTERING AGENT MAKING IT COMPATIBLE WITH OTHER OPERATIONS PERFORMED ON THE TEXTILE.

us. or. 874

TREATMENT OF CELLULOSIG TEXTILES WITH1,3-DIMETHYLOL-4,S-DIHYDROXY-Z-lMlDAZOL- IDINONE, ZlNC NITRATE AND ASEQUESTER- ING AGENT Robert Francis Bann, William Joseph Moran, andPhilip B. Roth, Bridgewater Township, Somerset County, N..l., assignorsto American Cyanamid Company, Stamford, Conn.

N Drawing. Continuation of abandoned application 5m.

No. 672,450, Oct. 3, 1967, which is a continuation-inpart of applicationSer. No. 628,573, Apr. 5, 1967. This application Feb. 10, 1971, Ser. No.114,380

lint. Cl. Dtl6p 5/02; Dtl6m 13/12, 13/34 4 Claims ABSTRACT OF THEDl'SCLOSURE A finish for cellulosic textile materials to give a wrinkleresistant and permanent crease to said textile materials, wherein thefinish contains a sequestering agent making it Compatible with otheroperations performed on the tex tile. 0

This application is a continuation 'of application Ser. No. 672,450,filed Oct. 3, 1967, now abandoned, which was a continuation-in-part ofapplication Ser.'No. 628,- 573, filed Apr. 5, 1967, now abandoned.

This invention relates to a nondiscoloring, durable press finish fordyed or undyed, cellulosic textile materials. More particularly, itrelates to a process of applying an aqueous finish containing1,3-dirnethylol-4,S-dihydroxy- 2-imidazolidinone of Formula I, azincnitrate catalyst and a sequestering agent to 'cellulosic materials, andto the treated cellulosic materials.

0 [I O 5, HOOH2N N CH;1)H- g-n f ff Etc-(:11: 01% OH (I) 1,3dimethylol-4,5-dihydroxy-Z-imidazolidinone is a very valuable finishingagent for textile materials. It has a wide and extensive use oncellulosic materials and blends of cellulosic materials with otherfibers such as polyamides (nylon) and polyesters (Dacron). It isgenerally used together with sodium acetate. Although it can be used asa conventional wash-and-wear finish, its greatest use is in the durablepress field, especially in the postcure process as described in US. Pat.No. 2,974,432. Zinc nitrate is the preferred curing catalyst. The finishhas not, however, been entirely satisfactory since it is not compatiblewith other operations performed on the textile materials. For example,it has been found that it causes scorching on white goods during thepressing operation and yellowing during the postcuring operation.

Moreover, it has not been found to be satisfactory for use with certainresin sensitive dyes such as a group of blue vat dyes based onindanthrone (Formula II) and Ice its chlorinated derivatives thereofwhich have considerable commercial values.

HN 0 0 [It] NH When a cellulosic fabric dyed with one of the indanthronedyes is treated with a textile finish containing 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, followed by a' curingoperation in the presence of zinc nitrate as the curing catalyst, theshade of the fabric is severely altered, becoming duller and muchgreener. The color change is so drasticfthat cloth dyed with one of theindanthrone dyes cannot, therefore, be treated with a wrinkle resistantfinish containing 1,3 dimethylol 4,5 dihydroxy-2 imidazolidinone andzinc nitrate.

Zinc nitrate is the preferred catalyst for use in curing 1,3dimethylol-4,5-dihydroxy-2-imidazolidinone. Other zinc salts, such aszinc chloride and zinc sulfate, do not produce the desired wash-and-wearproperties. Other curing catalysts, such as magnesium chloride, are alsonot as satisfactory as zinc nitrate and-are not used.

. Therefore, the need exists for a method of applying and heat curing atextile finish containing 1,3-dimethylol-4,5-dihydroxy-Z-imidaZolidinone with the zinc nitrate catalyst to give awrinkle resistant or permanent crease finish which is compatible withother operations, particularly with white cellulosic materials whichwill prevent 40 or reduce 1) yellowing on curing, and (2) scorching onhot pressing, and with cellulosic materials dyed with resin-sensitivedyes.

It is therefore an object of this invention to provide a finish and amethod for rendering cellulosic textile materials wrinkle resistant orproviding a permanent crease, said finish being compatible with otheroperations on said textile material.

A further object is to provide a method and finish for undyed cellulosictextile materials, incorporating1,3dimethylol-4,5-dihydroxy-Z-imidazolidinone and zinc nitrate, forobtaining wrinkle resistance or permanent creases on said textiles,which does not cause yellowing on curing or scorching on hot pressing orironing after washing.

Another object is to provide a method and finish for cellulosic textilematerials incorporating 1,3 dimethylol- 4,5-dihydroxy-2-imidazolidinoneand zinc nitrate, for obtaining wrinkle resistance or permanent creaseson said textiles, which does not discolor resin sensitive dyes on saidtextile materials.

A further object is to obtain an undyed textile material which iswrinkle resistant or permanently pressed and which does not yellow oncuring or scorch on pressin Another object is to obtain a dyed textilematerial which is Wrinkle resistant or permanently pressed and whereinthe shade is not discolored.

These and other objects of the invention will become apparent as thedescription thereof proceeds.

A method has now been discovered for applying 1,3- dimethylol 4,5dihydroxy-Z-imidazolidinone to undyed cellulosic materials which willprevent or reduce yellowing on curing and scorching on hot pressing andto dyed textile materials to prevent discoloration of the dye.

In the process of this invention an aqueous solution of 1,3-dimethylol4,5 dihydroxy 2 imidazolidinone, a sequestering agent, and zinc nitrateis applied to the cellulosic textile material. The textile material isthen dried and the finish is cured at an elevated temperature. In apostcure process, the dried fabric is made into a garment or otherarticle which is then pressed and cured.

Cellulosic textile material has the usual meaning and includes blendswith other fibers such as polyamides (nylon) and polyesters (Dacron),including woven, knitted, felted, or other textile goods, for example.

rSuitable sequestering agents for use in this invention are described involume 12, page 164, of Encyclopedia of Chemical Technology, firstedition, and in Organic sequestering Agents by Chaberek (1959).

The two principal classes of sequestering agents which are suitable arethe aminopolycarboxylic acids, such as ethylenediaminetetraacetic acid,nitrilotriacetic acid, di- (hydroxyethyl glycine, (hydroxyethyl)ethylenediaminetriacetic acid and diethylenetriaminepentaacetic acid,and the hydroxycarboxylc acids, such as gluconic acid, citric acid andtartaric acid. These are used as partially neutralized alkali metalsalts.

The resin sensitive dyes include certain dyes of several classes, suchas direct dyes, sulfur dyes, reactive dyes, disperse dyes, vat dyes, andparticularly indanthrone vat dyes.

The indanthrone dyes include indanthrone (C.I. Vat Blue 4, Cl. No.69800), dichloroindanthrone (C.I. Vat Blue 6, Q1. No. 69825),monochloroindanthrone (C.I. Vat Blue 14, C.I. No. 69810), mixture ofrnono-, diand trichloroindanthrones (C.I. Vat Blue 10, 0.1. No. 69830),etc.

The sequestering agent can be put on the cellulosic materialssimultaneously with, prior to or subsequent to the application of the1,3-dimethylol-4,5-dihydroxy-2- imidazolidinone and zinc nitrate. It ispreferred to apply the imidazolidinone, zinc nitrate and sequesteringagent from the same aqueous solution. However, the sequestering agentcan be applied from an aqueous solution before or after the applicationof the imidazolidinone and zinc nitrate.

The aqueous solution of 1,3-dimethylol-4,S-dihydroxy- Z-imidazolidinone,sequestering agent, and zinc nitrate is applied to the textile materialby any of the normal methods of application, such as by padding,spraying, dipping and the like.

The amount of 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone applied tothe textile materials should be between 1.0% and 25.0%, preferablybetween 3.0% and 8.0%, based on the weight of the textile material.

The amount of sequestering agent used should be between 0.05% and 3.0%,preferably between 0.15% and 1.0% based on the weight of the solution.This corresponds to between about 0.025% and 3.0%, preferably betweenabout 0.075% and 1.0%, based on the weight of the fabric.

The amount of zinc nitrate should be between 5.5% and 16.5%, preferablybetween 9.5% and 12.5%, based on the weight of the imidazolidinone.

The treated fabric may be dried and cured by conventional wash-and-wearprocedures. Also, the well known 4 postcuring procedure of U.S. Pat. No.2,974,432 can be used, which consists of drying the treated fabric;cutting, sewing and pressing the garment; and curing the finish on thegarment at an elevated temperature.

The treated textile material is normally dried before the pressing andcuring operations are performed. A drying temperature between and 250F., preferably between 200 and 225 F., is used. The pressing operationcan be done by any of the methods well known in the trade, such as bythe use of a hot head press. The pressing operation is carried out at atemperature of 300 to 420 F. In the curing operation, the pressed fabricis heated at an elevated temperature under conditions normally used bythe trade which is at a temperature between 300 and 420 F., preferablybetween 320 and 380 F., for a period suificient to react theimidazolidinone with the cellulosic fabric. Heating periods between 5and 20 minutes are normal.

The textile finish of this invention is compatible with many fluorescentbrightening agents normally used on cellulosic materials, particularlythe stilbene class of "brightening agents.

Undyed cellulosic fabrics treated by the process of this invention havegood resistance to scorching and discoloration when the fabrics arepressed and cured at elevated temperatures.

In one preferred embodiment of the invention with dyed fabrics, a cottonfabric dyed with an indanthrone vat dye is padded with an aqueoussolution containing about 9% ofl,3-dimethylol-4,S-dihydroxy-imidazolidinone, about 1% of zinc nitrateand about 0.35% of ethylenediaminetetraacetic acid, tetrasodium salt.The treated fabric, containing about 6% of the imidazolidinone is driedat 225 The dried fabric is then cut and sewed into garments which arepressed at about 310 F. The pressed garments are then heated in an ovenat about 340 F. until the imidazolidinone is cured on the garment. Thethus treated garment is durably pressed where creases are desired and iswrinkle resistant in those areas where wrinkles and creases are notdesired. 'During the pressing and drying operation the shade of the dyedfabric is essentially unchanged.

It has been discovered that the sodium acetate normally used in thefinish containing 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone todecrease the initial losses in tensile strength, tear strength andabrasion resistance is not required when the sequestering agent is used.Additionally, the sequestering agent appears to give more stable padbaths than sodium acetate. It has been found that the sequestering agentused in the invention does not cause precipitation of the fluorescentbrightening agents in finishing baths.

The following specific examples are set forth to illustrate theinvention and are not intended to be limitative.

In the following examples, the parts and percentages are by weight.

The nonionic surface active agent used in the examples is thecondensation product of nonylphenol with an average of 9.5 moles ofethylene oxide. Other suitable nonionic surfactants can also be used,such as other alkyl aryl polyethylene glycol ethers and ethylene oxideadducts of straight chain alcohols.

The fluorescent brightening agent used on undyed goods is C. I.Fluorescent Brightening Agent 25, a compatible brightening agent. It isa commercial product belonging to the sulfonated diaminostilbene classof brightening agents and was employed as an aqueous solution. Inaddition to this particular brightening agent, any other suitable onescan be used such as other members of the sulfonated diaminostilbeneclass, providing they are compatible with the other components of thefinish.

EXAMPLE 1 Eight aqueous pad baths were prepared, each bath containing11.2% of 1,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone, 1.25% of zincnitrate, 0.25% of a nonionic surface active agent, 0.5% of C. I.Fluorescent Brightening Agent 25, and sodium acetate or a sequesteringagent as shown in Table I. The pH of the pad baths was adjusted to 4.7by addition of sodium hydroxide or hydrochloric acid as required.

TABLE I Pad bath: Additive A None.

B 0.1% sodium acetate.

C 0.4% ethylenediaminetetraacetic acid,

tetrasodium salt.

'D 0.4% gluconic acid.

E 0.4% nitrilotriacetic acid.

F 0.4% diethylenetriaminepentaacetic acid,

pentasodium salt.

G 0.4% N,N-di(hydroxyethyl) glycine,

sodium salt.

H 0.4% (hydroxyethyl)ethylenediaminetriacetic acid, trisodium salt.

The pad baths were applied by standard padding procedure to a 65/35polyester/cotton fabric obtaining a 70% wet pickup. The fabrics,containing 7.9% on the weight of the fabric of1,3-dimethylol-4,S-dihydroxy-Z- imidazolidinone, were dried for 1 minuteat 225 F., steamed for 5 seconds, pressed for 5 seconds at 350 F., andheated in an oven at 320 F. for 8 minutes.

The fabrics were examined for discoloration by comparing the color ofthe treated fabrics with that of the untreated fabric.

The fabrics were laundered 5 times in a homestyle Washing machine usingwater at 130l40 F. and a detergent followed by a rinse water treatmentat about 110- 120 F. and tumble drying after each washing. The fabricswere then inspected for retention of creases placed in the fabric duringthe pressing operation.

The results are shown in Table II. Fabrics A-H corresond to pad bathsA-H, respectively.

TABLE II Discoloration Cease retention The above results demonstrate theeffectiveness of various sequestering agents in reducing thediscoloration of polyester/ cotton fabrics when treated with1,3-dimethylol- 4,5-dihydroxy-2-imidazolidinone and zinc nitrate.

EXAMPLE 2 Five aqueous pad baths were prepared, each bath containing8.0% of 1,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone, 0.80% of zincnitrate, 0.25% of a nonionic surface active agent, 0.5% of C. I.Fluorescent Brightening Agent 25 and sodium acetate or a sequesteringagent as shown in Table III. The pH of the pad baths was adjusted to 4.7by addition of hydrochloric acid as required.

acid, trisodium salt.

The pad baths were applied by standard padding procedure to cottonbroadcloth obtaining a 73% wet pickup. The fabrics, containing 5.8% onthe weight of the fabric of1,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone, were dried at 225 F. for1 minute. Swatches of the dried fabrics were cured for 1 minute at 360F.

The wrinkle recovery of the cured fabrics was measured by tentative testmethod 66-1959T of the American Association of Textile Chemists andColorists. The results are shown in Table IV. Fabrics A-E cor- Theseresults show the lack of adverse effect of the sequestering agents onthe wrinkle recovery properties of a cotton fabric treated with a finishcontaining 1,3-dimethylol-4,5-dihydroxy-Z-imidazolidinone.

EXAMPLE 3 Six aqueous pad baths Were prepared, each bath containing 8.6%of 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, 0.85% of zincnitrate, and sodium acetate or ethylenediarninetetraacetic acid,tetrasodium salt (EDTA) in the amounts shown in Table V. The pH of thepad baths containing EDTA were adjusted to 4.3 with hydrochloric acid.

TABLE V pH Additive .07% sodium acetate. EDTA.

The pad baths were applied by standard padding procedure to cottonbroadcloth which had been pre'brightened an preblued with an aqueoussolution containing 0.5% of CI. Fluorescent Brightening Agent 25, 0.03%of Cl. Vat Blue 6 and 0.25 of nonionic surface active agent.

The wet pickup was 70%. The fabrics, containing 6.0% on the weight ofthe fabric of 1,3-dimethylol-4,5-di-hydroxy-2-imidazolidinone, weredried for 1 minute at 225 F., steamed for 5 seconds and pressed for 5seconds at 350 F., an then heated in an oven for 8 minutes at 320 F.

The wrinkle recovery of the fabrics was measured as described in Example2. The laundering process is described in Example 1.

The tensile strength of the fabrics was measured by ASTM standard methodusing a Scott tensile strength tester.

The fabrics were inspected for discoloration by comparing the color ofthe treated fabrics with that of the untreated fabric.

The results are shown in Table VI. Fabrics A-F correspond to pad bathsA-F, respectively.

TABLE VI Wrinkle recovery, W & F, degrees Tensile After 5 strengthInitial washes (1b.) Discoloration 292 276 59 Severe. 296 284 62 S1ight.289 299 59 Do 297 297 66 Very slight. 290 277 71 Do. F 289 284 72 Do.Untreated 214 181 136 Do.

7 EXAMPLE 4 TABLE VII pH Additive Pad bath:

4. 7 0.074% sodium acetate. 4.3 0.20% ED'IA.

4.3 0.25% EDTA 4.3 0.30% EDIA 4.3 0.35% EDTA 4.3 0.40% EDIA The padbaths were applied by standard padding procedure to 65/35polyester/cotton shirting prebrightened and preblued as described inExample 3, obtaining a Wet pickup of 65%. The fabrics, containing 5.6%on the weight of the fabric of 1,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone, were dried for 1 minutes at 225 F., steamed seconds andpressed for 5 seconds at 350 F., and then heated in an oven for 8minutes at 320 F.

The fabrics were inspected for discoloration and retention of creasesafter 5 launderings as described in Example 1.

The results are shown in Table VIII. Fabrics A-F correspond to pad bathsA-F, respectively.

TABLE VIII Crease re- Discoloration tention EXAMPLE 5 TABLE IX pHAdditive Pad bath:

A None.

0.07% sodium acetate.

The pad baths were applied to (1) cotton broadcloth and (2) 65/ 35polyester/ cotton shirting by standard padding procedures with a 70% wetpickup on the cotton fabric and a 65% Wet pickup on the polyester/cottonfabric. The fabrics containing 6.0% on the weight of the fabric oncotton and 5.6% on the polyester/cotton fabric of1,3-dirnethylol-4,5-dihydroxy-Z-imidazolidinone were dried for 1 minuteat 225 F., steamed for 5 seconds, pressed for 5 seconds at 350 F., andthen heated in an oven for 8 minutes at 320 F.

The fabrics were inspected for discoloration as described in Example 1.

The results are shown in Table X. Fabrics A-I correspond to pad bathsA-I, respectively.

TABLE X Diseoloration Cotton Polyester cotton 5 Fabric A Severe Severe.B.-. do. Do. 0. --do Do. D. oderat D0. E- Slight... Moderate F. Veryslight-- Slight. 10 G do Very slight.

H -d0 Do. I do Do.

EXAMPLE 6 Six aqueous pad baths were prepared, each bath containing theamounts of 1,3 dimethylol 4,5-dihydroxy- Z-imidazolidinone and zincnitrate shown in Table XI, 0.25% of a nonionic surface active agent,0.5% of Cl. Fluorescent Brightening Agent 25, and the amount of sodiumacetate or N,N-di(hydroxyethyl) glycine, sodium salt (DEG) shown inTable XI. The pH of the pad baths is also shown in Table XI.

TABLE XI Imidazo- Zinc lidinone, nitrate,

percent percent pH Additive 4. 3 0. 43 4. 9 0.037% sodium acetate. 4.30. 43 4.7 0.25% DEG. 7.9 0. 79 4. 8 0.068% sodium acetate. 7.9 0.79 4.70.46% DEG. 11.5 1. 4. 6 0.099% sodium acetate.

11. 6 1. 30 4. 7 0.68% DEG.

The pad baths were applied to cotton broadcloth by standard paddingprocedure with a 70% wet pickup. The fabrics containing the amount of1,3-dimethylol-4,5-dihydroxy 2 imidazolidinone shown in Table XII weredried at 225 F. for 1 minute. Swatches of the dried fabrics were (1)heated at 320 F. for one minute, (2) heated at 360 F. for one minute or(3) steamed for 5 seconds, pressed for 5 seconds at 350 F., and thenheated at 320 F. in an oven for 8 minutes.

The wrinkle recovery of the swatches heated for 1 minute at 320 F. or360 F. was measured by the procedure of Example 2.

The swatches steamed, pressed and heated at 320 F. were inspected fordiscoloration by the procedure of Example 1.

The results are shown in Table XII. Fabrics A-F correspond to pad bathsA-F, respectively.

5 TABLE XII Imidazolidi- Wrinkle recovery none percent W & F, degreesat- (on weight oi fabric) 320 F. 360 F. Discoloration 3. 0 231 236Slight. 3. 0 217 230 Do. 5.5 243 209 Moderate. 5.5 233 273 Slight. 8. 0286 288 Severe. 8.0 279 270 Slight.

EXAMPLE 7 9 TABLE XIII Pad bath: Additive A 0.07% sodium acetate. B 0.2%NTA. C 0.1% NTA. D 0.05% NTA. E 0.025% NTA.

The pad baths were applied to cotton broadcloth by standard paddingprocedure with a 70% wet pickup. The fa brics containing 6.0% on theweight of the fabrics of 1,3 dimethylol 4,5 dihydroxy 2 imidazolidinonewere dried for one minute at 225 C. Swatches of the dried fabric were 1)heated at 320 F. for 1 minute, (2) heated at 360 F. for 1 minute, or (3)steamed for 5 seconds, pressed for 5 seconds at 350 F., and then heatedin an oven at 320 F. for 8 minutes.

The wrinkle recovery of swatches heated for 1 minute at 320 F. or 360 F.were measured by the procedure of Example 2.

The swatches steamed, pressed and heated at 320 F. were inspected fordiscoloring by the procedure of Example 1.

The relative fluorescent intensity, a measurement of brighteneractivity, was measured by standard procedure using a fluorimeter.

The results are shown in Table XIV. Fabrics A-E correspond to pad bathsA-E, respectively.

TABLE XIV Wrinkle recovery W & F, degrees Fluorescent intensity, 320 F.360 F. Discoloration percent Fabric A 277 280 Severe 100 273 273 276 E261 Untreated 202 EXAMPLE 8 Five pad baths were prepared, each bathcontaining 8.6% of 1,3 dimethylol-4,5-dihydroxy-Z-imidazolidinone, 0.85%of zincnitrate, 0.25% of a nonionic surface active agent, 0.5% of C.I.Fluorescent Brightening Agent 25 and the amount of sodium acetate ornitrilotriacetic acid (NTA) shown in Table XV. The pHs of the pad bathscontaining NTA were adjusted to 4.7 with sodium hydroxide. Pad bathcompatibility was noted after 8 hours. Two of the pad baths were allowedto stand 16 hours before application to fabric.

TABLE XV Pad bath Pad bath stored for Additive compatibility 16 hoursPad bath:

A 0.07% sodium acetate- Very cloudy No. B 0.3% NTA Clear Yes 0---"--- 02% NTA-- D. 0.3% NT E- 0.2% NTA-..

The pad baths were applied to cotton broadcloth by the procedure ofExample 7. The wrinkle recovery, discoloration and fluorescent intensitywere measured by the method of Example 7.

The results are shown in Table XVI. Fabrics A-E cor- 1 0 EXAMPLE 9- Twopad baths were prepared, each bath containing 9.0% of1,3-dimethylol-4,5-dihydroxy2-imidazolidinone, 0.96% of zinc nitrate,0.75% of a polyethylene emulsion containing polyethylene glycolmonostearate and coconut oil ethanolamine (a commercial textilesoftener), 0.2% of a nonionic surface active agent, and the amount Thepad baths were applied by standard padding procedure to x 80 cottonpercale dyed with 3.0% on the weight of the fabric of an indanthronedye, C.I. Vat Blue 6 (C.I. No. 69,825) obtaining a 70% wet pick-up. Thefabrics, containing 6.3% on the weight of the fabric of 1,3-dirnethylo14,5 dihydroxy-Z-imidazolidinone, were dried at 225 F. for one minute,pressed for 15 sec. at 310 F., and heated in an oven at 340 F. for 10minutes.

The fabrics were examined for shade change by comparing the treatedfabrics with untreated dyed fabric.

The fabrics were laundered five times in a home-style washing machineusing water at F. and tumble drying after each washing. The fabrics werethen inspected for retention of creases placed in the fabric during thepressing operation.

The results are shown in Table XVIII. Fabrics A and B correspond to PadBaths A and B, respectively.

TABLE XVIII Crease Shade change retention Fabric:

Definite Excellent. B. Negligible Do.

EXAMPLE 10 TABLE XIX Pad bath: Citric acid A None. B 0.7%.

The pH of the pad baths was adjusted to 4.7 by the addition of sodiumhydroxide.

The pad baths were applied by standard padding procedure to 80 x 80cotton percale dyed with 3.0% on the weight of the fabric of anindanthrone dye, C.I. Vat Blue 6 (C.I. No. 69825), obtaining an 80% wetpick-up. The fabrics, containing 9.0% on the weight of the fabric of1,3-dimethylol 4,5 dihydroxy-Z-imidazolidinone; were dried at 225 F. forone minute, steamed for 5 seconds, pressed for 15 seconds at 310 F., andheated in an oven at 380 F. for 6 minutes.

The fabrics were examined for shade change by comparing the treatedfabrics with untreated dye fabrics. The durable press properties of thetwo fabrics were also determined.

The results are shown in Table XX. Fabrics A and B correspond to PadBaths A and B, respectively.

TABLE XX Durable Shade change press Fabric:

A Definite Excellent. B None Do.

1 1 In the use of citric acid as the sequestering agent, sufficientsodium hydroxide is added to provide a pH of between about 4.5 and 5.5,preferably 4.7 to 4.9.

EXAMPLE 11 TABLE XXI Citric acid,

percent pH of bath Pad bath:

A 4. 5 B 0 7 4.0 C 0 7 4.5

The pad baths were applied by standard padding procedure to white cottonbroadcloth obtaining a 75% wet pick-up. The fabrics, containing 8.5% onthe weight of the fabric ofl,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone, were dried at 225 F.,steamed for 5 seconds, pressed for 5 seconds at 350 F., and heated in anoven at 320 F. for 8 minutes.

The wrinkle recovery of the fabrics was measured by the procedure ofExample 2. The fabrics were inspected for discoloration by the procedureof Example 1.

The results are shown in Table XXII. Fabrics A, B and C correspond toPad Baths A, B and C, respectively.

TABLE XXII Wrinkle recovery W+F, degrees Discoloration 2915 Severe. 304Moderate. 295 Slight.

EXAMPLE 12 TABLE XXIII Appearance Discoloration Fabric A Good Severe..do Moderate C do Slight.

While certain specific embodiments and preferred modes of practice havebeen set forth, this is solely for purposes of illustrating theinvention, and it will be obvious that various changes and modificationsmay be made without departing from the spirit of the disclosure and thescope of the appended claims.

We claim:

1. A process for producing a non-discoloring, wrinkle resistant finishon cellulosic textile materials, said materials being subject todiscoloration of resin sensitive dyes thereon or yellowing on curingconsisting essentially of: forming a treated cellulosic textile byapplying one or more aqueous solutions of1,3-dimethylol-4,S-dihydroxy-Z-imidazolidinone, zinc nitrate and asequestering agent thereto; drying the treated textile; and curing thedried textile by heating for a period sufiicient to cause theimidazolidinone to react with the cellulose textile; wherein the amountsof the l,3-dimetl1yl0l-4,5-dihydr0xy 2 imidazolidinone and sequesteringagent applied to said cellulosic textile are in the range of 1.0% and25.0% and between about 0.025% and 3.0%, respectively, based on theweight of the fabric, and the amount of zinc nitrate is between 5.5% and16.5% based on the weight of the imidazolidinone; the drying temperatureis between F. and 250 F.; the curing temperature is between 300 F. and420 F. whereby a non-discoloring, wrinkle resistant finish is producedon the cellulosic textile.

2. A process according to claim 1 wherein the textile to be treated hasan indanthrone dye thereon.

3. A cellulosic textile material, subject to discoloration of resinsensitive dyes thereon or yellowing on curing, having a non-discolored,wrinkle resistant finish thereon by application of the heat curedproduct of 1,3-dimethylol- 4,5-dihydroxy-2-imidazo1idinone and asequestering agent in amounts in the range of 1.0% and 25.0% and betweenabout 0.025 and 3.0%, respectively, based on the weight of the fabric,and zinc nitrate in an amount of between 5.5% and 16.5% based on theweight of the imidazolidinone.

4. A textile according to claim 3 wherein the textile to be treated isindanthrone dyed.

References Cited UNITED STATES PATENTS 3,183,195 5/1965 Hushebeck 8116.3X 3,186,954 6/1965 Hushebeck 81 16.3 X 3,029,164 4/1962 Seki et al.8116.3 X 3,458,271 7/1969 Ito et al. 8--18 3,501,259 3/1970 Long 8-18OTHER REFERENCES Ziifle et al.: Investigation of the Catalyst in theCellulose-DMEU Reaction, Part II, Physicochemical Studies of theReaction, Journal of Applied Polymer Science, vol. 7, 1963, pp.1041-1053 and 1060.

Chaberek et al.: Organic Sequestering Agents," 1959, Wiley & Sons, pp.322-324, 329, 330, 334, 335.

ROLAND E. MARTIN, 1a., Primary Examiner US. Cl. X.R.

